Let's consider how a methyl group is involved in hyperconjugation with a carbocation centre. | |
First we need to draw it to show the C-H s-bonds. Note that the empty p orbital associated with the positive charge at the carbocation centre is in the same plane (i.e. coplanar) with one of the C-H s-bonds (shown in blue.) | |
This geometry means the electrons in the s-bond can be stabilised by an interaction with the empty p-orbital of the carbocation centre. (this diagram shows the similarity with resonance and the structure on the right has the "double bond - no bond" character) |
Of course, the C-C s-bond is free to rotate, and as it does so, each of the C-H s-bonds in turn undergoes the stabilising interaction.
So the ethyl cation has 3 C-H s-bonds that can be involved in hyperconjugation.
The more hyperconjuagtion there is, the greater the stabilisation of the system.
So for example, the t-butyl cation has 9 C-H s-bonds that can be involved in hyperconjugation. Hence (CH3)3C+ is more stable than CH3CH2+
The effect is not limited to C-H s-bonds, appropriate C-C s-bonds can also be involved in hyperconjugation.
So the ethyl cation has 3 C-H s-bonds that can be involved in hyperconjugation.
The more hyperconjuagtion there is, the greater the stabilisation of the system.
So for example, the t-butyl cation has 9 C-H s-bonds that can be involved in hyperconjugation. Hence (CH3)3C+ is more stable than CH3CH2+
The effect is not limited to C-H s-bonds, appropriate C-C s-bonds can also be involved in hyperconjugation.
No comments:
Post a Comment